Hilton Head Island, January 22, 2026
StayTerra’s recent investment in Vacation Homes of Hilton Head aims to strengthen the local tourism industry by leveraging technology and enhancing service offerings. Founded by local entrepreneurs, Vacation Homes of Hilton Head has established itself as a leader in luxury vacation rentals, focusing on quality management and local staffing. This partnership symbolizes confidence in Hilton Head’s economy and highlights the significant opportunities present for growth in the competitive short-term rental market.
Hilton Head Island
StayTerra Fuels Local Growth with Investment in Vacation Homes of Hilton Head
A significant private investment in Vacation Homes of Hilton Head by StayTerra is poised to bolster the island’s thriving tourism sector, highlighting the power of entrepreneurial vision and strategic capital in driving local economic expansion. This collaboration is expected to enhance service offerings and leverage technological advancements for continued growth in the competitive short-term rental market.
In a testament to the enduring appeal and robust economic opportunities within Hilton Head SC business, StayTerra, a prominent vacation rental platform, recently announced its investment in Vacation Homes of Hilton Head (VHHH). This move signifies more than just a corporate transaction; it represents a vote of confidence in the local economy and the dedicated entrepreneurs who have built successful enterprises on the island. Such private investments are crucial in fostering a dynamic business environment, enabling local companies to scale, innovate, and contribute further to the region’s prosperity without excessive regulatory burdens.
The investment, announced on January 21, 2026, marks StayTerra’s fourth brand acquisition in approximately a year, strategically expanding its presence along the southeastern Atlantic coast. This expansion into a market as vital as Hilton Head underscores the appeal of destinations that offer a clear path for business growth and a welcoming environment for both visitors and investors.
A Legacy of Local Entrepreneurship
Vacation Homes of Hilton Head was founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski. Their journey exemplifies the spirit of local entrepreneurship, building a company dedicated to managing a portfolio of luxury vacation rental homes on the island. VHHH has earned a distinguished reputation for its meticulous property care, commitment to local staffing, and the implementation of technology-enabled pricing and management strategies. This focus on quality and innovation has allowed them to generate superior revenue for property owners and maintain a loyal base of returning guests. The company’s dedication to providing exceptional experiences is further highlighted by its concierge services and the exclusive Southern Hospitality Pass, offering guests complimentary local activities.
StayTerra’s Strategic Vision for Vacation Rentals
StayTerra positions itself as a collection of premier vacation rental brands dedicated to providing best-in-class property management for owners and elevated guest experiences across top destinations in America. Launched in 2024, the platform aims to be the leading choice for vacation rentals, driven by a commitment to outstanding customer service, integrity, and hospitality. Supported by strategic growth investments from Bessemer Venture Partners and existing investor Garnett Station Partners, StayTerra is well-equipped to execute its vision for market expansion and technological integration. Its portfolio already includes notable brands such as Cape & Coast Premier Properties, AMI Locals, Anna Maria Vacations, Siesta Key, Lido Key Vacations, and Siestakey Tropical Sands in Florida, alongside Moving Mountains in the Colorado Rockies.
The investment in Vacation Homes of Hilton Head presents a significant opportunity for StayTerra to expand its footprint on Hilton Head Island and the surrounding areas. For VHHH, integrating with the StayTerra platform is anticipated to foster additional growth by providing access to capital, advanced technology, and enhanced operational support, all while preserving its distinct brand identity and local operational expertise. This partnership demonstrates how larger entities can invest in and empower successful Hilton Head small business, allowing them to thrive and contribute more substantially to the Beaufort County economy.
Hilton Head’s Dynamic Short-Term Rental Market
Hilton Head Island continues to solidify its position as one of the most established leisure markets in the U.S., attracting more than three million visitors annually. This vibrant tourism economy makes it a significant destination for vacation rentals and ranks it among the top 10 beach destinations for families nationwide. The market experiences a strong summer season, complemented by robust shoulder seasons, ensuring consistent demand for accommodations.
The broader trend of short-term rental growth has seen demand increase nationwide by nearly 20% since 2018, with South Carolina experiencing over 17% growth in the same period. Within South Carolina, Hilton Head ranks among the metropolitan regions with the largest annual impacts from short-term rental markets. These rentals contribute substantially to the South Carolina SC entrepreneurs and property owners, generating an estimated $1.8 billion in revenue annually across the state, a figure that has more than doubled since 2018. The overall annual economic impact of short-term rentals in South Carolina is estimated at $4.2 billion, supporting over 50,000 jobs and more than $1.4 billion in labor income for South Carolinians.
Economic Indicators and Future Outlook
Recent data further illustrates Hilton Head Island’s economic vitality. In 2024, tourism revenue reached an impressive $2.8 billion, driven by 2.8 million visitors. The island also saw the opening of 160 new businesses in 2024, bringing the total number of active businesses to 2,514. Furthermore, the Hilton Head Island Airport experienced a 9.5% increase in traffic since 2023, signaling continued interest and visitation.
The short-term rental market specifically on Hilton Head Island shows compelling performance metrics. There are 7,042 registered short-term rental units, primarily concentrated on the island’s south end. While summer 2023 saw occupancy rates at 47% (a decrease from 56% the previous year), the average daily rate for rentals increased by 4% to $815. Other data points to an average daily rate of $484 with a 3% increase over the past year, and an occupancy rate of 59% with a 4% increase, contributing to an annual revenue of $51.1K with 3% growth. The peak revenue month for short-term rentals on Hilton Head Island is typically July, with January marking the lowest revenue period. This robust and growing market, despite fluctuations, suggests that investing in Hilton Head property, where the median home price hovers around $730,000, can be a lucrative choice.
Community Insights and Economic Benefits
The ongoing growth and strategic investments in sectors like vacation rentals underscore the positive impact of private enterprise on Hilton Head economic growth. These developments not only enhance the visitor experience but also create jobs, stimulate local businesses, and generate tax revenue that benefits the entire community. By facilitating the expansion of companies like Vacation Homes of Hilton Head through strategic partnerships, the island reinforces its reputation as a premier destination and a fertile ground for business success.
This investment highlights the confidence in Hilton Head’s economic future and the entrepreneurial spirit that continues to define its business landscape. Supporting local businesses and understanding the dynamics of private investment are key to maintaining the island’s vibrant economy and ensuring sustained prosperity for all its residents and visitors.
Frequently Asked Questions
- What is StayTerra?
- StayTerra is a platform comprised of premier vacation rental brands in top destinations across America. It was established in 2024 and focuses on providing best-in-class property management for owners and elevated experiences for guests.
- What is Vacation Homes of Hilton Head?
- Vacation Homes of Hilton Head (VHHH) is a luxury property management company operating on Hilton Head Island, South Carolina, founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski. The company manages a portfolio of luxury vacation rental homes and is known for its focus on property care, local staffing, and technology-enabled pricing and management.
- What does StayTerra’s investment in Vacation Homes of Hilton Head mean?
- StayTerra’s investment in Vacation Homes of Hilton Head, announced on January 21, 2026, marks the fourth brand added to the StayTerra platform and expands the group’s presence into the southeastern Atlantic coast. For VHHH, this partnership is expected to support further growth through access to capital, technology, and operational support, while retaining its existing brand identity and local presence.
- How many visitors does Hilton Head Island attract annually?
- Hilton Head Island is one of the most established leisure markets in the U.S., attracting more than three million visitors annually.
- What is the estimated annual economic impact of short-term rentals in South Carolina?
- The annual economic impact of short-term rentals on the state of South Carolina is estimated to total approximately $4.2 billion annually.
Key Features of StayTerra’s Investment in Vacation Homes of Hilton Head
| Feature | Description |
|---|---|
| Acquirer | StayTerra |
| Acquired Company | Vacation Homes of Hilton Head (VHHH) |
| Announcement Date | January 21, 2026 |
| Significance for StayTerra | Fourth brand added to its platform, expanding presence to the southeastern Atlantic coast. |
| Significance for VHHH | Expected to support further growth through access to capital, technology, and operational support, while retaining its local presence. |
| VHHH Founding | Founded in 2008 by Hilton Head natives Chris and Jacquelyn Sankowski. |
| VHHH Focus | Manages luxury vacation rental homes with an emphasis on property care, local staffing, and tech-enabled management. |
| Hilton Head Tourism | Attracts over three million visitors annually and is a top 10 beach destination for families in the U.S. |
| South Carolina STR Economic Impact | Estimated at $4.2 billion annually, supporting 50,231 jobs and over $1.4 billion in labor income. |
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Author: STAFF HERE HILTON HEAD
The HILTON HEAD STAFF WRITER represents the experienced team at HEREHiltonHead.com, your go-to source for actionable local news and information in Hilton Head Island, Beaufort County, and beyond. Specializing in "news you can use," we cover essential topics like product reviews for personal and business needs, local business directories, politics, real estate trends, neighborhood insights, and state news affecting the area—with deep expertise drawn from years of dedicated reporting and strong community input, including local press releases and business updates. We deliver top reporting on high-value events such as the RBC Heritage golf tournament, Hilton Head Island Wine & Food Festival, and the Gullah Celebration. Our coverage extends to key organizations like the Hilton Head Island-Bluffton Chamber of Commerce and Community Foundation of the Lowcountry, plus leading businesses in tourism and hospitality that power the local economy such as Sea Pines Resort and Sonesta Resort Hilton Head Island. As part of the broader HERE network, including HEREAiken.com, HEREBeaufort.com, HEREChapin.com, HERECharleston.com, HEREClinton.com, HEREColumbia.com, HEREGeorgetown.com, HEREGreenwood.com, HEREGreenville.com, HEREHiltonHead.com, HEREIrmo.com, HEREMyrtleBeach.com, HERENewberry.com, HERERockHill.com, and HERESpartanburg.com, we provide comprehensive, credible insights into South Carolina's dynamic landscape.
